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Cyanamide → 2-(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}-3-fluorophenyl)ethyl imidocarbamate triflate

HRID 474594
Notes
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Reaction equation

HRID 474594 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][C:10]=2[F:18])=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20].[N:23]#[C:24][NH2:25].[F:26][C:27]([F:33])([F:32])[S:28]([OH:31])(=[O:30])=[O:29]>C1COCC1>[OH:31][S:28]([C:27]([F:33])([F:32])[F:26])(=[O:30])=[O:29].[C:24](=[NH:23])([O:17][CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:19]([F:22])([F:20])[F:21])[CH:4]=2)=[C:10]([F:18])[CH:11]=1)[NH2:25]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 9864CyanamideHCID 62406Trifluoromethanesulfonic acidHCID 677742772-(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}-3-fluorophenyl)ethanol

Product 1

HCID 866661992-(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}-3-fluorophenyl)ethyl imidocarbamate triflateYield 23.82%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
60 °C

Procedure

To the solution of 2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-3-fluorophenyl)ethanol (4.0 g, 11.95 mmol) and cyanamide (0.603 g, 14.34 mmol) in anhydrous THF (25 mL) was added trifluoromethanesulfonic acid (2.55 mL, 28.7 mmol) at 0° C. The reaction mixture was stirred at 60° C. for 4 h. Purification via a reverse phase Biotage then afforded the title compound as a white solid (1.5 g, 23.82% yield). LCMS: rt=3.68 min, [M+H+]=377

Workup

  1. customPurification via a reverse phase Biotage

Sources & evidence

ORD record
ord-7074ca6d20f346c2be3fac0eb7c3d367
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08637536B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes